My most popular download of all time is My 100 Best Sales Questions. If you don't already have your copy, I'll include a link at the bottom of the page. Right now, let's look at the problem at hand. How can we get our salespeople to ask the right question at the right time? You can do it while coaching 1:1 or in one to many training.

In a 1:1...

Start debriefing a real, recent sales call with a rep. What happened then? What did they say? What happened then? What did they say? What happened then? What did they say? Get your rep comfortable with the rhythm. You'll be able to tell they're getting comfortable because their answers will come quicker and smoother. When you're ready ask, "Why did they say that?" Be prepared for them to be caught off guard and answer, "I don't know." Help, by asking, "If you had to guess?" When they give you an answer, ask, "OK. Why else might they have said that?" Keep asking until you've got a few answers. If they need help, you can ask, "Could it be that ... ?" When you have a selection of possible reasons for the prospect's reply, ask your rep, "So, which is it?"

They'll have three possible answers.

"I don't know."

"Could be any or all of them."

They'll pick one.

Your response is, "How can we know for sure?"

You need your rep to say, "Ask them?"

You reply, "Ask them what?"

"Ask them why they said that?"

You then ask, "...but what has to happen before you ask them?"

Hopefully, your rep will answer, "Ask them if I could ask them a question?"

Your reply is, "Even before that."

"I don't know."

"Don't you have to ask yourself, 'Why did they say that?'"

That's the lesson: Before your rep asks a drill-down question, they have to ask themselves why their prospect just said what they said and again and again and again...

If you're doing a group training, rather than asking your rep, "OK. Why else might they have said that?" you ask all the other reps in the room.

BTW, this IS how I coach. 3-5 15 minute calls/week. Debrief one situation per call just like this. The only difference is that I'll take a minute to make sure they understand which of their core competencies is getting in the way.

If you need to get your team's core competencies evaluated, start here.